You Are Trying To Break My Heart

October 7, 2009 8:10 AM

What are your picks for melancholy, lonely, time-stopping and heartachingly beautiful songs?

I'm looking for other songs that fit the same vibe as these:

Eddie Vedder - The Long Road
Neil Young - Helpless
Otis Redding - I've Been Loving You Too Long (To Stop Now)
Peter Murphy - Cuts You Up
Fleetwood Mac - Songbird
REM - Everybody Hurts or You Are The Everything or Me in Honey
My Morning Jacket - Golden or Gideon
Death Cab For Cutie - I Will Follow You Into the Dark
The Decemberists - Eli The Barrow Boy
Eva Cassidy - Autumn Leaves

Basically any song that just makes you sit with it and take a musical time-out, and gets your chest a little tight in that good way.

All genres and styles welcome.

posted by Lipstick Thespian to media & arts (223 answers total)

Mercury Rev - The Dark Is Rising
posted by randomination at 8:14 AM on October 7, 2009

Oh god.

Definitely The Blower's Daughter by Damien Rice. You can check it out on YouTube. It kills me a little bit but in a good way.
posted by kbanas at 8:18 AM on October 7, 2009 [3 favorites]

Neutral Milk Hotel - Two Headed Boy (actually the entire album, In the Aeroplane Over the Sea, but you asked for song titles)
posted by heyho at 8:19 AM on October 7, 2009

Ootischenia by The Be Good Tanyas.
posted by workerant at 8:20 AM on October 7, 2009

Pearl Jam: Low light
posted by effluvia at 8:20 AM on October 7, 2009

Pete Yorn - "Lose You"
Magnetic Fields - "Book of Love"
posted by dlugoczaj at 8:20 AM on October 7, 2009 [1 favorite]

Tom Waits - Tom Traubert's Blues
Luna - Superfreaky Memories
And this from MeFite gmm. The 'our feelings... equal true' bit in the robot voices is just lovely.
posted by permafrost at 8:21 AM on October 7, 2009

Josh Radin-- Winter
Dry Branch Fire Squad-- Devil, Take the Farmer
Simon and Garfunkel-- For Emily, Wherever I May Find Her; The Dangling Conversation

posted by Bardolph at 8:22 AM on October 7, 2009 [1 favorite]

Please Don't Go, by Barcelona.

Definitely stops time. My (deceased) daughter loved fish and would have loved to watch the aquarium in the link. Okay, see, now I am already crying, 1:27 into the song.
posted by bunnycup at 8:23 AM on October 7, 2009 [1 favorite]

Seas Too Far to Reach by Okkervil River..or really anything from their older albums.
posted by minicloud at 8:23 AM on October 7, 2009

Great suggestions on the NMH and Mercury Rev - I have both of those releases and they are exactly what I'm on about in this thread. More, more!
posted by Lipstick Thespian at 8:25 AM on October 7, 2009

Almost the entire corpus of Nick Drake
posted by IndigoJones at 8:25 AM on October 7, 2009 [2 favorites]

Ali Harter's Grandpa does it to me everytime.

Cowboy Junkies' The Last Spike will hit anyone who comes from a small, dying town. Sorry, can't find a full version online.

(I also like their cover of Neil Young's Powderfinger, which fits your criteria, too. My favorite version.)
posted by rokusan at 8:25 AM on October 7, 2009

Bjork - "All Is Full of Love"
Linda Perhacs - "Chimacum Rain"
posted by dlugoczaj at 8:26 AM on October 7, 2009

Chalet Lines by Belle & Sebastian.
Asleep by the Smiths
posted by Admiral Haddock at 8:27 AM on October 7, 2009

Martin Sexton - Where Did I Go Wrong
Christine Lavin - The Kind of Love You Never Recover From
Rufus Wainwright - Foolish Love
posted by mikepop at 8:27 AM on October 7, 2009 [1 favorite]

Ben Folds - Carrying Cathy
Travis - Circle
October Project - Johnny
Mary Fahl - Lenses of Contact
Anna Nalick - Breathe
posted by xingcat at 8:27 AM on October 7, 2009

Elvis: Unchained Melody. Prepare to cry.
posted by effluvia at 8:28 AM on October 7, 2009

Sarah McLachlan's version of Unchained Melody always gets me. And I hate that song.
posted by hollygoheavy at 8:28 AM on October 7, 2009

The Smiths made a career out of this sot of thing. "There is a light that will never go out" from the end of their career to "That joke isn't funny anymore" at the start.

The Tindersticks "Tiny Tears" is lovely.

This is going to be a long thread...
posted by Fiery Jack at 8:29 AM on October 7, 2009 [2 favorites]

Rufus Wainwright - Harvester of Hearts
posted by legendarygirlfriend at 8:30 AM on October 7, 2009

oops, forgot the link for Where Did I Go Wrong
posted by mikepop at 8:31 AM on October 7, 2009

Ooo, I forgot about Tiny Tears by the Tindersticks. I haven't listened to that one in awhile. It's also very, very good. Nice one, Fiery Jack.
posted by kbanas at 8:32 AM on October 7, 2009

Crap, the Travis song is called Side.
Also, anything by Richard Thompson.
And Telstar by the Tornados is sad to me, but that may just be me.
posted by xingcat at 8:32 AM on October 7, 2009

Tom Waits' song Time. And dammit, even though it's become nigh-unto cliche by now, the James Buckley cover of Cohen's Hallelujiah.

(I respond big-time to lyrics, and something about Waits growling, "It's time, time, time that you loved...." or Cohen's "all I ever learned from love/is how to shoot at someone who outdrew you" just undo me.)
posted by EmpressCallipygos at 8:36 AM on October 7, 2009

Jets To Brazil - Further North

Built To Spill - Untrustable/Pt. 2 (About Someone Else) this is not the whole song - you want the album cut off of "Perfect From Now On")

Michael Penn - Figment

The Promise Ring - Things Just Getting Good

The Wedding Present - Dalliance

The Ataris - Looking Back On Today
posted by namewithoutwords at 8:36 AM on October 7, 2009

Bob Seger - We've Got Tonight
Vince Gill, Patty Loveless, Ricky Skaggs - Go Rest High on that Mountain
posted by Sassyfras at 8:36 AM on October 7, 2009

Fiona Apple - Never is a Promise
Rachael Yamagata - Quiet
Margot & the Nuclear So & So's - A Light on a Hill
posted by non sum qualis eram at 8:37 AM on October 7, 2009

I listen to Elliott Smith as this quality pervades most of his music. Highlights, in my opinion: Somebody That I Used To Know, Needle in the Hay (I can't stand it, but it's one of his most acclaimed songs), Waltz #2.
posted by wackybrit at 8:37 AM on October 7, 2009

Silent in the Morning by Phish -- just a beautiful song.
posted by MustardTent at 8:38 AM on October 7, 2009

No Surprises by Radiohead. It's on OK Computer. Truly music to have a nice cry over.
posted by elder18 at 8:38 AM on October 7, 2009 [2 favorites]

Blue - Leann Rimes
You Were Meant For Me - Jewel
Crazy - Patsy Cline
Hurt - Johnny Cash
I'm Not In Love - 10cc
posted by torquemaniac at 8:38 AM on October 7, 2009

DeVotchKa - How it Ends
posted by gaspode at 8:39 AM on October 7, 2009 [2 favorites]

I forgot to mention Radiohead - How To Disappear Completely - maybe the "loneliest" and despair-ridden song I've ever heard. I'm not sure it gets me in a "good" way, but I still find it heart-achingly beautiful.
posted by wackybrit at 8:40 AM on October 7, 2009 [3 favorites]

sorry - here are the links

Go Rest High on that Mountain

We've Got Tonight.

Hey - thanks for making me cry today!
posted by Sassyfras at 8:43 AM on October 7, 2009

Calling All Angels, by Jane Siberry.
posted by rtha at 8:44 AM on October 7, 2009

The Low Anthem - "Charlie Darwin"

Nearly brings tears to my eyes, every time.
posted by grapefruitmoon at 8:45 AM on October 7, 2009 [1 favorite]

Radiohead - Pyramid Song
Unkle - Lonely Soul

I absolutely second Nick Drake. Try, for instance, Day is Done.
posted by ourobouros at 8:45 AM on October 7, 2009

(Oh man, Calling All Angels, that song DOES make me cry. I need tissues just THINKING about it.)
posted by grapefruitmoon at 8:45 AM on October 7, 2009

The Arcade Fire - Crown of Love
Elvis Presley - Love Me Tender
The Skyliners - Since I Don't Have You (covered by many artists)
The Beatles - Long Long Long
John Lennon - Mother
Ben Folds Five - Boxing
Nine Inch Nails - Something I Can Never Have
posted by Jaltcoh at 8:45 AM on October 7, 2009

Also: Tori Amos' cover of "Thunder Road."
posted by grapefruitmoon at 8:46 AM on October 7, 2009

Dylan - Tomorrow is such a long time
Kate Rusby - Who Will Sing Me Lullabies?
posted by Freedomboy at 8:46 AM on October 7, 2009

The Wrens - She Sends Kisses (and really most of the rest of the Meadowlands album)
Counting Crows - Anna Begins
posted by substars at 8:47 AM on October 7, 2009

oh, forgot:

Simon and Garfunkel - Bridge over Troubled Water
posted by Jaltcoh at 8:47 AM on October 7, 2009

Elbow's "August and September" (originally done by The The, but heartbreakingly covered by Elbow).
posted by MonkeyToes at 8:50 AM on October 7, 2009

I don't know the name of this song or the artist and but this song is lovely and haunting. I found it at The Late Greats and the author of the blog couldn't provide any identifying information, either. But seriously, great song.

Bob Dylan - Red River Shore
David Berkeley - Fire Sign
Fred Eaglesmith - Drive-In Movie
Greg Brown - Banjo Moon
Iron & Wine - The Trapeze Swinger
Matt Bauer - Don't Let Me Out
Michael Johnson - Ghost In This House
Nanci Griffith - Late Night Grande Hotel
Romantica - La Traviada
posted by diamondsky at 8:50 AM on October 7, 2009

New Order, In a Lonely Place. Even sadder once you know the backstory.
posted by googly at 8:52 AM on October 7, 2009

"Middle Cyclone" by Neko Case from her eponymous album.
posted by The Michael The at 8:52 AM on October 7, 2009 [1 favorite]

Some that immediately come to mind for me:
Joanna Newsom Sawdust and Diamonds
PJ Harvey White Chalk
Bruce Springsteen Reason to Believe
Low Murderer
posted by otolith at 8:53 AM on October 7, 2009

Leavin' on a Jet Plane - Peter Paul & Mary

Crying - Roy Orbison (also worth finding the Roy Orbison/k.d. lang duet version on YouTube)

Slip Sliding Away - Paul Simon

Mr. Tanner - Harry Chapin
posted by DevilsAdvocate at 8:53 AM on October 7, 2009

Jeff Buckley's cover of Hallelujah.
posted by robocop is bleeding at 8:55 AM on October 7, 2009 [3 favorites]

Ane Brun's cover of "True Colors."

Ryan Adams' cover of "Wonderwall."

Gary Jules' cover of "Mad World."

Bon Iver's Creature Fear."
posted by MuffinMan at 8:56 AM on October 7, 2009 [1 favorite]

Damien Rice - 9 Crimes
posted by grapefruitmoon at 8:57 AM on October 7, 2009 [1 favorite]

Jeff Buckley - Lover, You Should Have Come Over
posted by legendarygirlfriend at 8:57 AM on October 7, 2009 [1 favorite]

And because I am undercaffeinated:

Birdland, by Patti Smith

The Kid, covered by Cry Cry Cry.

Pretty much anything from Cry Cry Cry's album, really.

Orphan Girl, by Gillian Welch.

Vincent Black Lightning 1952, by Richard Thompson.
posted by rtha at 8:59 AM on October 7, 2009

MIKA - Happy Ending
The Verve - History
posted by gnomeloaf at 8:59 AM on October 7, 2009

This one totally kills me every time I hear it...major goose bumps right now.

When Somebody Loved Me
.
posted by Xoebe at 9:00 AM on October 7, 2009 [2 favorites]

One Day Like This, by Elbow
Skinny Love by Bon Iver
The Calendar Hung Itself by Bright Eyes
I Do Dig a Certain Girl by Devendra Banhart
Freedom Hangs Like Heaven by Iron & Wine
Ballad for My One True Love by Mason Jennings
Eyes by Rogue Wave
The One You Love by Rufus Wainwright (though that might be more of a good driving song)
Amour Fou by Vetiver
[June] Under a Honeymoon by The Good Life (a really post-breakup good album to listen to as a whole)

And definitely anything by Nick Drake. That poor man.
posted by runningwithscissors at 9:02 AM on October 7, 2009

OH, and Clam Crab Cockle Cowrie by Joanna Newsom.
posted by The Michael The at 9:02 AM on October 7, 2009

Neil Young's Harvest Moon /tears
posted by Xoebe at 9:06 AM on October 7, 2009

Iron and Wine - Naked as We Came, Dead Man's Will
Townes Van Zandt - St. John the Gambler
Lyle Lovett - Step Inside This House
Linda Thompson - Day after Tomorrow
posted by notsnot at 9:10 AM on October 7, 2009

Most anything by Red House Painters/Mark Kozelek, specifically You Ain't got a Hold on Me, Song for a Blue Guitar, Michael, and Grace Cathedral Park.
posted by esmerelda_jenkins at 9:10 AM on October 7, 2009

I See a Darkness -- Bonnie Prince Billy or Johnny Cash
This Year's Love -- David Gray
At My Window Sad and Lonely -- Billy Bragg & Wilco
Fool of Me -- Me'Shell Ndege Ocello
Martha -- Tom Waits
Lonely Sinking Feeling -- Cowboy Junkies
Good Woman -- Cat Power
The River -- Bruce Springsteen
posted by dhn at 9:11 AM on October 7, 2009 [2 favorites]

My goto is Barenaked Ladies, but it might be too ballad-y for you.

Break My Heart, When I fall, What a Good Boy, War on Drugs, Tonight is the Night I Fell Asleep At the Wheel

(hope the quality is at all decent, I don't have flash at work so I didn't vet the videos)
posted by politikitty at 9:12 AM on October 7, 2009 [1 favorite]

Lux Arumque - Eric Whitacre
posted by tylerfulltilt at 9:14 AM on October 7, 2009

My Morning Jacket - I will be there when you die
Leonard Cohen - Famous Blue Raincoat
Billie Holliday - Gloomy Sunday
Empyrium - When Shadows Grow Longer
posted by prufrock at 9:15 AM on October 7, 2009 [1 favorite]

This one has been tearing at me lately - it's just haunting:
Imogen Heap - Hide and Seek

For something completely different, this one has always gotten to me:
The Stranglers - Princess of the Streets

The last one is about my soon-to-be ex-wife. It's the only thing that makes me feel anything at all about her.

Why are you making me cry at nine o'clock in the morning?
posted by Xoebe at 9:15 AM on October 7, 2009 [1 favorite]

Yann Perreau's L'ange sur la mezzanine is pretty haunting.
posted by fish tick at 9:17 AM on October 7, 2009

Elizabeth Cotten - Freight Train
posted by not_on_display at 9:17 AM on October 7, 2009

If you enjoy Eva Cassidy, you will probably love Nancy LaMott. Tragically she also died of cancer, one year before Ms. Cassidy, but she recorded a wealth of incredible music before she died. Specific songs that fit your parameters are:

Autumn Leaves/When October Goes (the arrangement blends the two expertly)
How Deep is the Ocean
I Have Dreamed

Also, the album Nancy LaMott: Live at Tavern on the Green is a recording of her last performance, complete with stage banter, done just seven weeks before she died. She explains her decision to forgo the standard "gut-wrenching ballad" portion of the show, stating that she's had enough of that in real life. She ends her set with "Help is on the Way" and as her encore sings a phenomenal rendition of "The Secret of Life [is enjoying the passage of time]" If the song itself isn't enough to break your heart, the knowledge that it is the last one she ever recorded is. The entire album is heartachingly beautiful, both in musicality and as a result of the circumstances surrounding its recording.
posted by philotes at 9:18 AM on October 7, 2009 [1 favorite]

This thread over here is a "saddest songs ever" thread. So it overlaps your question a good bit. I put a bunch there but will just highlight one of them here: Song to the Siren by This Mortal Coil. Good GOD! Wear headphones. Close your eyes.
posted by kookoobirdz at 9:21 AM on October 7, 2009 [1 favorite]

Oh, did somebody call me?

Charlie Rich - Feel Like Going Home (the demo version)
Neil Finn - Sinner
Cracker - Dr. Bernice
Cowboy Junkies - The Way I Feel
Warren Zevon - Keep Me In Your Heart (for the whole thing, but especially for "I'm tied to you like the buttons on your blouse.")
Oh Susanna - Back Dirt Road
Holger Czukay - Persian Love
Tom Waits - Hold On
Beth Orton - Blood Red River
The Handsome Family - Weightless Again
Them/Van Morrison - It's All Over Now Baby Blue (sorry, tacky video)
Blue Rodeo - 5 Days in May
posted by maudlin at 9:24 AM on October 7, 2009 [1 favorite]

for me, it's Led Zeppelin's No Quarter and, coincidentally, off the same album, The Rain Song
posted by Redhush at 9:27 AM on October 7, 2009

Radiohead - How to Disappear Completely
posted by Lutoslawski at 9:28 AM on October 7, 2009

Lykke Li - Melodies and Desires

I ache when I hear this.
posted by Unicorn on the cob at 9:29 AM on October 7, 2009

Apparently I didn't read your question correctly the first time around. I stick by the Nick Drake suggestion, though. Also try "Be Good or Be Gone" by Fionn Regan.
posted by runningwithscissors at 9:32 AM on October 7, 2009

Lots of songs by the Wailin' Jennys. Try Prairie Town. (Lots more on the website.)
Hope There's Someone by Antony & The Johnsons
Smoky Mountain Memories by Dolly Parton
Bill Frisell's Blues Dream has a ton of great songs that fit the bill (try What Do We Do? or check out his version of Shenandoah for something a little different)
Yours and Mine by Calexico (sorry, can't find a link)
Love Won't Last the Afternoon by David Poe
Homesick by the Kings of Convenience (bonus: amusing intro to the video)
Sunflower by Low
Lost Verses by Sun Kil Moon (maybe my favorite)
posted by dseaton at 9:33 AM on October 7, 2009 [2 favorites]

The Weepies, "World Spins Madly On" (or just about anything, really; it's like their agent told them they'd have to live up to that name...)

Rufus Wainwright, "The Art Teacher"

Colin Hay, "I Don't Think I'll Ever Get Over You"

Patty Griffin, "Long Ride Home"
posted by Madamina at 9:35 AM on October 7, 2009 [1 favorite]

See also this MeFi post. Permit me to mention "At Seventeen" again.
posted by fish tick at 9:40 AM on October 7, 2009 [2 favorites]

Bruce Springsteen - Meeting Across The River
Bruce Springsteen - Racing In The Street
Bruce Springsteen - The River
Tom Waits - Christmas Card From A Hooker In Minneapolis
Tom Waits - Kentucky Avenue
Liz Phair - Divorce Song
Tom Waits and Crystal Gayle - Is There Any Way Out Of This Dream?
Tom Waits and Crystal Gayle - Picking Up After You [this video is an early studio outtake with not Crystal Gayle]
Pretenders - My Baby [this video is a River Phoenix tribute, so unless you're into him look away while you listen to Chrissie's ringing guitars]
Cake - End Of The Movie
Cake - I Will Survive [the loping tempo and sleepy vocal really get me on this one, along with what I hear as the seething Townshend-esque anger in the two-note guitar solo. Not to mention the subtle salt of profanity.]
Pete Townshend - Slit Skirts
posted by chazlarson at 9:43 AM on October 7, 2009

You're a Big Girl Now - Bob Dylan
posted by watercarrier at 9:43 AM on October 7, 2009

Anything from The Antlers - Hospice album, especially Kettering.
posted by dantekgeek at 9:46 AM on October 7, 2009

Jolie Holland - Mehitabel's Blues
posted by twistofrhyme at 9:46 AM on October 7, 2009

Brand New - Jesus
posted by relucent at 9:46 AM on October 7, 2009

Ryan Adams- Come Pick Me Up
posted by banjo_and_the_pork at 9:48 AM on October 7, 2009 [2 favorites]

Sufjan Stevens - "Casimir Pulaski Day"

Duncan Sheik - "Hey Casanova," "The Dawn's Request," "Hymn," "Nothing Fades" (all from the "White Limousine" album). "Far Away" from the "Phantom Moon" album.

Glad someone already mentioned Jane Siberry's "Calling All Angels." If you like that you might also like by her: "The Valley" and "Love is Everything." (K.D. Lang has also covered those.)

Seriously - watch that "Love is Everything" video I linked there. Whew.
posted by dnash at 9:49 AM on October 7, 2009

Oh Jesus, how did I forget Calexico? When "Missing" comes on, I shut the office door and prepare for shivers.
posted by notsnot at 9:53 AM on October 7, 2009 [1 favorite]

About a third or half of Jim Croce's greatest hits, but in particular, Photographs and Memories.

And seconding Warren Zevon's "Keep Me In Your Heart."
posted by kimota at 9:55 AM on October 7, 2009

Sebadoh's Brand New Love
posted by 23skidoo at 9:57 AM on October 7, 2009

Snow Patrol (featuring Martha Wainwright) - Set The Fire To The Third Bar

..gives me chills. every. time.
posted by jmnugent at 9:58 AM on October 7, 2009 [2 favorites]

"I'll Be Seeing You" - Judy Collins
posted by jgirl at 9:59 AM on October 7, 2009

Okkervil River- Kansas City and Listening to Otis Redding at Home During Christmas
Sam Cooke - Bring It On Home To Me
Bon Iver - For Emma
Nina Nastasia - That's All There Is
Phosphorescent - A Picture Of Our Torn-Up Praise
Neko Case - This Tornado Loves You (already mentioned, but worth seconding) and Star Witness
Songs: Ohia - Being In Love
Gillian Welch - Revelator
Clem Snide - 1989
Earlimart - Happy Alone
Cass McCombs - I Went To The Hospital
Casiotone For The Painfully Alone - New Year's Kiss
posted by sarabeth at 9:59 AM on October 7, 2009 [2 favorites]

I so agree with, You're a Big Girl Now. Also,

Neil Young - Comes a Time (acoustic version on Live Rust)
Will Oldham - I am a Cinematographer
Will Oldham - Allowance
posted by phelixshu at 9:59 AM on October 7, 2009

Many of the Grateful Dead's versions of Morning Dew. The linked version is from the '80's, but my favorite version comes from the end of 5.22.77, available on Dick's Picks 3. It's devastating.

The Cowboy Junkies' version of Lost My Driving Wheel.
posted by pasici at 10:01 AM on October 7, 2009

Also adding Water From The Same Source by Rachel's. There aren't any words, but it's so lonely and beautiful and makes my heart swell.
posted by sarabeth at 10:01 AM on October 7, 2009 [1 favorite]

Warren Zevon's "Searching for a Heart." Not to be confused with "Keep Me in Your Heart."
posted by dortmunder at 10:02 AM on October 7, 2009

"Valentine" by The Get Up Kids
"Hear You Me" by Jimmy Eat World
"This is the Sea" by The Waterboys
"Keep Me In Your Heart" by Warren Zevon
posted by timdicator at 10:07 AM on October 7, 2009

Hawksley Workman - Safe and Sound
posted by legendarygirlfriend at 10:08 AM on October 7, 2009

• Nina Simone: "I Loves You Porgy"
• Bill Evans: "I Loves You Porgy"
• Loren Connors: "Star of Bethlehem"
• Talk Talk: "I Believe in You"
• Blossom Dearie: "Some Other Time"

posted by ryanshepard at 10:09 AM on October 7, 2009

Angel from Montgomery, as performed by Bonnie Raitt and John Prine
posted by SuperSquirrel at 10:10 AM on October 7, 2009 [2 favorites]

Love Will Tear Us Apart by Joy Division

Why is the bedroom so cold
Turned away on your side?
Is my timing that flawed,
Our respect run so dry?
posted by Dali Atomicus at 10:11 AM on October 7, 2009

Lipstick, you will like this ... Massive Attack's "Teardrop".
posted by Dave. at 10:12 AM on October 7, 2009

This might not have aged well and I don't have speakers to listen but I used to sit down and listen to Sam Brown/Stop. Can't believe no-one's mentioned Sinead O'Connor's Nothing Compares (but it might be as untrendy as I am to do so ;-)
posted by ceri richard at 10:14 AM on October 7, 2009

John Prine - The Great Compromise, Sam Stone, and Hello in There

Ben Folds - Smoke and Brick

The Concretes - New Friend

Warren Zevon - The French Inhaler and Hasten Down the Wind

David Bowie - Five Years

Billy Bragg - The Saturday Boy

Catch 22 - As the Footsteps Die Out Forever
posted by ghharr at 10:14 AM on October 7, 2009

Richard Thompson - God Loves a Drunk
Jason Isbell - Dress Blues
John Prine - Angel From Montgomery
Tom Paxton - The Last Thing on My Mind
posted by louche mustachio at 10:14 AM on October 7, 2009

Lord I'm Discouraged - The Hold Steady
Breathe Me - Sia
My Body is a Cage - Arcade Fire
posted by clearly at 10:17 AM on October 7, 2009 [1 favorite]

Oh good grief, Xeobe, way to make me bawl like a baby. Really, it's just the allergy to dusty onions, I'm totally not weeping at a kids' movie.

Kwoon's I Lived on the Moon also tears me up regularly.
posted by Jilder at 10:17 AM on October 7, 2009

Sia - Breathe Me
Jeff Buckley - Lover, You Should've Come Over
The Rolling Stones - Wild Horses
Fiona Apple and Elvis Costello - I Want You

Mmm, yeah.
posted by rachaelfaith at 10:35 AM on October 7, 2009

Gulf Coast Highway by Nanci Griffith and always makes me pretty weepy.
posted by vespabelle at 10:37 AM on October 7, 2009

Gram Parsons and Emmylou Harris - Love Hurts
The Everly Brothers - Let It Be Me
The Beach Boys - Don't Talk (Put Your Head On My Shoulder)
posted by dfan at 10:38 AM on October 7, 2009

More from Songs:Ohia - Coxcomb Red, though I'm partial to the Joe Beats remix, part of a wonderfully moody Indie Rock Blues re-mix-tape.
posted by filthy light thief at 10:39 AM on October 7, 2009 [1 favorite]

Oh, what about Roberta Flack - The First Time Ever I Saw Your Face? Gets me every time.
posted by sciapod at 10:42 AM on October 7, 2009 [1 favorite]

Innocence Mission - I Never Knew You From the Sun

Counting Crows - Raining in Baltimore
posted by MeetCleaverTheatre at 10:52 AM on October 7, 2009

The Mekons' "Last Dance" (not to be confused with the disco hit, thank you). It's in waltz time! I can listen to it over and over and over and over.

The Flamin' Groovies' "Shake Some Action."

Bowie's "Heroes."

Seconding Hold Steady's "Lord I'm Discouraged."

Husker Du's cover of the Byrds' "Eight Miles High" improves on the original IMHO. [ducks projectiles] It brings out so much sorrow in the song where the Byrds (again, IMHO) stick to sheer trippiness.

Skip James's "Devil Got My Woman" is also suffused with sorrow. Such an amazing voice.

I feel sad now and I must stop this.
posted by scratch at 10:53 AM on October 7, 2009 [1 favorite]

Arcana - The Song of Solitude (The Cry of Isolde), from their album Cantar De Procella. A portion of the song can be found here.

So beautiful that it gives me chills within the first ten seconds. No matter how I might try, I cannot stay dry-eyed when I hear it.
posted by velvet winter at 10:56 AM on October 7, 2009

Oh oh oh I forgot "Fourth of July" by X. About a dissolving relationship. I've always suspected it was une chanson a clef.
posted by scratch at 10:56 AM on October 7, 2009

Host of Seraphim by Dead Can Dance

Since you opened it up to all genres:
Ase's Death from Peer Gynt Suite #1 by Grieg
Piano Sonata #14 ("Moonlight") by Beethoven
Vesti La Giubba from Pagliacci by Leoncavallo
Nessun Dorma from Turandot by Puccini
Adagio in G Minor by Albinoni
posted by joaquim at 11:03 AM on October 7, 2009 [1 favorite]

Motion Picture Soundtrack - Radiohead
Videotape - Radiohead
Now At Last - Feist
Old Man - Randy Newman
Acid Tongue - Jenny Lewis
I Fought in a War - Belle & Sebastian
posted by bingwah at 11:07 AM on October 7, 2009

It's actually on my "Murderers" playlist, but I still think Amy LaVere's Killing Him (Didn't Make the Love Go Away) qualifies.

(Can't find the studio version sorry.)
posted by rokusan at 11:14 AM on October 7, 2009

Sinead O'Connor - Last Day Of Our Acquaintance
George Jones-He Stopped Loving Her Today
My Morning Jacket - Librarian
Bob Dylan Blind Willie McTell
The Pogues & Kirsty McColl - Fairytale Of New York
LCD Soundsystem - All My Friends
posted by pianomover at 11:15 AM on October 7, 2009

Nothing Compares 2 U – Sinead O’Connor
Unloved – Jann Arden and Jackson Browne
I Love You – Sarah McLachlan
Goodbye, My Lover – James Blunt
Only You - Yaz
So Cruel – U2
Gravity - Sara Bareilles
posted by yawper at 11:17 AM on October 7, 2009

Also:
Ugly Casanova Smoke Like Ribbons
Nina Nastasia How Will You Love Me
Neko Case I Wish I was the Moon
posted by otolith at 11:21 AM on October 7, 2009

Otolith mentioned Springsteen, which would never occur to me, but now that you mention it, pretty much all of the incredible Nebraska album, starting with the haunting title track, is one big heart ripper-outer.
posted by rokusan at 11:22 AM on October 7, 2009

Try Susanna and the Magical Orchestra's cover of "Love Will Tear Us Apart."

Also strongly seconding "Casimir Pulaski Day." Makes me cry, but I always feel cleansed afterwards.

Oh and ...

Feist - "Let It Die"
Metric - "Calculation Theme"
Otis Redding - "These Arms of Mine"

And the ace in the hole as far as "melancholy, lonely, time-stopping and heartachingly beautiful" goes has to be Nick Cave's "Into My Arms." I mean as far as I can tell, the music video is a bunch of people listening to the song and weeping.
posted by Devika at 11:25 AM on October 7, 2009 [1 favorite]

Maybe not heartbreaking in the way you want, but I find these beautiful:

Bonobo - Something ( Longer ) For Windy, from the Flutter EP.

Squarepusher - Iambic 5 Poetry, from the Budakhan Mindphone mini-album.
posted by filthy light thief at 11:29 AM on October 7, 2009

Low Shame
Morphine Gone For Good
posted by otolith at 11:32 AM on October 7, 2009 [1 favorite]

Pretty much any/all Smiths songs. I like "Please Please Please Let Me Get What I Want" and "Back to the Old House" a lot.
posted by chunking express at 11:39 AM on October 7, 2009

Casiotone for the Painfully Alone "Tonight Was a Disaster"
Bobby Birdman "All Right" and "All Right (Reprise)"
Jason Anderson "O, Jac!"
Heatmiser "Not Half Right"
Feist "Leisure Suite (Red Demo)" (has to be the red demo version! album version is...not good)
Elvis Costello "I Want You"
Ed Harcourt "Until Tomorrow Then"
Cat Power "Don't Blame You"
Beck "Everybody's Gotta Learn Sometime" (from the Eternal Sunshine o.t. S.M soundtrack)
Kind of Like Spitting "The Thing About Distance"
M. Ward "Undertaker"
posted by haveanicesummer at 11:39 AM on October 7, 2009

Son Volt - "Out of the Picture" although a ton of Son Volt stuff would fit your request.
posted by dbolll at 11:39 AM on October 7, 2009

Joel Plaskett - Love This Town
Okkervil River - Listening to Otis Reading at Home During Christmas
Weezer - Butterfly
Wilco - The Lonely One
Cat Power - Sea of Love
Drive-By Truckers - Goddamn Lonely Love and World of Hurt
Jimi Hendrix - The Wind Cries Mary
Jeff Buckley or Cohen - Hallelujah
posted by Midnight Rambler at 11:45 AM on October 7, 2009 [2 favorites]

Bob Dylan: If You See Her Say Hello

Seconding Bowie's Five Years.
posted by marxchivist at 11:47 AM on October 7, 2009

Teitur's The Singer.
posted by BrokenEnglish at 11:48 AM on October 7, 2009

Previously on le green. Also "Quicksand" by Bowie, off of Hunky Dory; "Do It Alone" by Jennifer Trynin, and Willie Nelson's version of "Always On My Mind".
posted by Halloween Jack at 11:50 AM on October 7, 2009

Right Where It Belongs - Nine Inch Nails

(also: Hurt by Nine Inch Nails. it's the same song suggested above except by NIN)
posted by majikstreet at 11:58 AM on October 7, 2009

This has been posted before, but Henryk Gorecki's 3rd Symphony as performed by Dawn Upshaw is one of the most heartbreakingly powerful peices of music out there. I defy anyone to keep a dry eye during a dedicated listen. Beautiful. Depressing, but beautiful.
posted by elendil71 at 12:04 PM on October 7, 2009

Allison Moorer, Is Heaven Good Enough For You is the saddest song I know.

This performance of Coldplay's Fix You, by an elderly gentleman singing what was supposed to be a duet, is probably the second-saddest.
posted by Clambone at 12:12 PM on October 7, 2009

I've never been able to listen to Neil Finn's Last to Know without getting a lump in my throat. (In fact, much of his album One Nil fits the bill.)
posted by scody at 12:15 PM on October 7, 2009

Love Love Love by the Mountain Goats
posted by Alison at 12:15 PM on October 7, 2009

Jon Hopkins' Light Through The Veins. Very repetitive - basically it's a single theme throughout the entire ~7 minute song. However, I found that after several listens it became a tune that I listen to over and over again - I have an idea to put a video/still slideshow of my kid to it. Can't explain why I like it, but I just do. It has almost taken over from Tangerine Dream's "Song of the Whale II - To Dusk.." as my favourite mental escape song. No lyrics (I hate them.)
posted by tra at 12:28 PM on October 7, 2009

rachael yamagata- meet me by the water
amanda palmer- have to drive
madeleine peyroux- damn the circumstances
allison krauss- doesn't have to be this way
cat power- the greatest
a fine frenzy- ashes and wine
stars- going going gone (live)
kathleen edwards- sweet little duck
dorval- ne me demande rien
isabelle boulay- je t'oublierai
sarah slean- last year's war
emily haines- reading in bed
marry me jane- you didn't kiss me
the sundays- when i'm thinking about you
remioromen- 粉雪/konayuki
portishead- roads
fra foa- 青白い月 aojiroi tsuki (worth mentioning that this one NEVER fails to make me cry. it was written for the singer's brother, who drowned when she was a child. you need to understand japanese to really get the full heartbreaking affect, but it will probably still hit you even if you don't)
posted by raw sugar at 12:29 PM on October 7, 2009

Vonda Shepard performing The End of the World.

Ally McBeal is on DVD now. Find the episode where this song is featured.

I dare you not to cry.
posted by misha at 12:29 PM on October 7, 2009

The original and the Poi Dog Pondering cover of The 13th Floor Elevators' "I Had To Tell You"

And someone mentioned Fiona Apple up the thread. The truth is every single song on When the Pawn... stops me in my tracks. (shhh, don't tell anyone)
posted by eyeballkid at 12:57 PM on October 7, 2009 [1 favorite]

Sigur Rós- Sæglópur
Radiohead - Weird Fishes / Arpeggi
Sufjan Stevens - John Wayne Gacy, Jr and Seer's Tour
posted by LakesideOrion at 12:59 PM on October 7, 2009

Sylvia's Mother, Dr. Hook (aka Shel Silverstein and the gang). I could wish for better audio quality in this video, but it's one of my favorites for all the backstory that's NOT spelled out.
posted by misha at 1:05 PM on October 7, 2009 [1 favorite]

Oh, here's Bon Jovi doing Sylvia's Mother!
posted by misha at 1:12 PM on October 7, 2009

Cowboy Junkies - I'm so lonesome I could cry
posted by googlebombed at 1:18 PM on October 7, 2009

The Low Anthem: pretty much anything, but try Ticket Taker; (Don't) Tremble; For the Ghosts Who Write History Books; This God Damn House.
The Duke and the King: One More American Song; Water Spider.
Tom Waits: I Hope That I Don't Fall in Love with You
Nikki Sudden: Farewell, My Darling (featuring Jeff Tweedy)
Tim Buckley: It Happens Every Time
Noah and the Whale: Do What You Do; Give a Little Love
Magnetic Fields: Come Back from San Francisco; Book of Love; many more
Glasvegas: It's My Own Cheating Heart that Makes Me Cry
Swans: God Damn The Sun.
posted by Infinite Jest at 1:19 PM on October 7, 2009

Ray LaMontagne - Let It Be Me
Marvin Gaye - Here, My Dear
Jeff Buckley - Lover, You Should Have Come Over
Dusty Springfield - Just A Little Lovin
Donny Hathaway - A Song For You
Rachel Yamagata - Meet Me By The Water
Meiko - How Lucky We Are
Meshell Ndegeocello - Love Song #2, Thankful
Amel Larriux - For Real
Melanie Fiona - You Stop My Heart
Corinne Bailey Rae - Call Me When You Get This
Alice Smith - Dream
Jewel – 1000 Miles Away
posted by heartquake at 1:23 PM on October 7, 2009

Two I should have added:

The Sleepers: "Linda" (here)
Big Star: "Try Again" (here)
posted by ryanshepard at 1:30 PM on October 7, 2009

"Almost Lover" - A Fine Frenzy
posted by Gotham at 1:31 PM on October 7, 2009

Chocolate Genius - My Mom
posted by KevinSkomsvold at 1:32 PM on October 7, 2009

And I'll add Hem's 'Leave Me Here' from "Rabbit Songs".

"Tonight he brought me to heaven and left me there."
posted by elendil71 at 1:43 PM on October 7, 2009

I love "Golden," I think it's a really underrated song.

Desperado, sung by 9-year-old Sheila Behman, in the Langley Schools Music Project.

Listen to this NPR interview with her and the schools' music teacher, ~25 years after the recordings, for Double the Heartbreak.

Also:

"100,000 Fireflies" by the Magnetic Fields
"I Burn Today" by Frank Black
"I Know It's Over" by the Smiths
"When I Was Drinking" by Hem
"All I Want" or "The Last Time I Saw Richard" by Joni Mitchell
"Alone Again Or" by Love

Seconding: Skinny Love, Star Witness, Into My Arms, Martha, and anything from In the Aeroplane Over the Sea

(I'm more of a lyrics person - most of the songs that really slay me do so through their words.)
posted by granted at 1:46 PM on October 7, 2009 [2 favorites]

Baby Bitch by Ween always gets me.

Cat Power, as mentioned upthread, has many of these types of songs. I dig Metal Heart off Moon Pix.
posted by waitangi at 1:53 PM on October 7, 2009

To go along with suggestions from upthread (Travis' "Side" and Johnny Cash's version of "Hurt"), I'll add on Driftwood by Travis, and Cash's cover of One.
posted by dnesan at 2:12 PM on October 7, 2009

"Parachutes" by mates of state
"Opus 40" by mercury rev
posted by snofoam at 2:41 PM on October 7, 2009

the ballad of love & hate (specifically this live version)
tear down the house
the lowering

all by the avett brothers, who are phenomenal at heart-wrenching music.
posted by thisiswater at 2:55 PM on October 7, 2009

Perhaps Brian Eno's "An Ending (Ascent)"?
posted by aheckler at 2:57 PM on October 7, 2009

The Owls - Air.
posted by Terheyden at 2:59 PM on October 7, 2009 [1 favorite]

I really really really love Ryan Adams' vocals on "200 More Miles" by the Cowboy Junkies.
posted by GamblingBlues at 3:27 PM on October 7, 2009

Grapefruit Moon by Tom Waits. Simply beautiful.
posted by Mrevilbreakfast at 3:30 PM on October 7, 2009

Jason Webley has a number: With, Almost Time to Go, It's Not Time to Go Yet, Goodbye Forever Once Again, Train Tracks, and Absinthe Makes the Heart Grow Fonder (a beautiful song despite the pun).

raw sugar already mentioned Amanda Palmer's "Have to Drive" above, but there's also Another Year: A Short History of Almost Something, and from her band the Dresden Dolls there's Delilah and Me and the Minibar.

My other suggestions have pretty much all been mentioned.
posted by Caduceus at 3:30 PM on October 7, 2009

Edith Piaf - Non, Je Ne Regrette Rien
The Beautiful South - I'll Sail This Ship Alone
posted by pompomtom at 3:31 PM on October 7, 2009

Little Willie John - You hurt me

I'm so glad I found this gem online
posted by ouke at 3:35 PM on October 7, 2009

Sleep Station - "There She Goes" (best heard in the narrative context of the full EP 'Von Cosel' - available for free download here)
Dan Fogelberg - "Leader of the Band" (Live in '91)
Kate Bush - "This Woman's Work"
Gene Clark - "With Tomorrow"
Keith Jarrett - "Sun Bear Concerts, Tokyo Encore (improvisation)"
Bonnie Raitt - "I Can't Make You Love Me"
posted by prinado at 3:37 PM on October 7, 2009

Mumford & Sons - White Blank Page

Alison Krauss + Union Station - New Favorite

Yeah Yeah Yeahs - Skeletons

Yeah Yeah Yeahs - Maps
posted by bibliophibianj at 3:49 PM on October 7, 2009

I Will Wait for You - Connie Francis (but only if you've seen the episode of Futurama in which it's featured)
posted by DevilsAdvocate at 3:59 PM on October 7, 2009

Annie Lennox -Why (I finally found a good older version)
Lisa Loeb -Stay
Blue Rodeo - House Of Dreams
Jimmy Buffett - He Went To Paris (great lyrics)
The Grapes Of Wrath - All The Things I Wasn't (nice video on this one; the first to use this seamless transition effect, I think)
Heart - Dog and Butterfly
Sarah McLachlan - Ben's Song (saved the best for last.)
posted by Hardcore Poser at 4:55 PM on October 7, 2009

Primitive Radio Gods - Standing Outside a Broken Phone Booth (With Money In My Hand)
Thirteen Senses - Into the Fire
Tom McRae - Mermaid Blues
Matthew Good Band - Sort of a Protest Song
posted by saveyoursanity at 7:13 PM on October 7, 2009

"G.T.O." (scroll down) by The Fellow Travelers, former band of Jeb Loy Nichols.
posted by HopperFan at 7:42 PM on October 7, 2009

DevilsAdvocate, noooo, now I've got that song in my head again. I bawl every time I even think about that episode.
posted by HopperFan at 7:46 PM on October 7, 2009

Sufjan Stevens - For the Widows in Paradise, For the Fatherless in Ypsilanti, Holland
Cat Stevens - Into White, Sad Lisa
Simon and Garfunkel - April Come She Will, The Dangling Conversation
Neil Young - Old Man
Joni Mitchell - River
Tori Amos - Winter
Bodies of Water - I Guess I'll Forget the Sound, I Guess I Guess
Crosby, Stills, & Nash - Helplessly Hoping
Many, many things by Elliot Smith, but my favorite is Angeles
Also many, many things by Nick Drake, including Saturday Sun
The Decemberists - Shiny
Donovan - Jersey Thursday
The Mountain Goats - Pale Green Things
REM - Texarkana
Pearl Jam - Immortality
Dar Williams - If I Wrote You
Indigo Girls - Kid Fears
Regina Spektor - Samson
Morrissey - Everyday Is Like Sunday
posted by naoko at 8:11 PM on October 7, 2009

David Grey's This Year's Love and Say Hello, Wave Goodbye.
Bob Dylan's Moonshiner and Kingsport Town ("Who's a gonna kiss your Memphis lips when I'm out in the wind? . . . Who's gonna look you straight in the eye and hold your bad luck hand?" The little portrait of true love and what happens when someone is left alone that this song paints makes me cry every time.).
Radiohead's Exit Music for a Film.
posted by onlyconnect at 8:35 PM on October 7, 2009

3rding jeff buckley - lover, you should've come over.
posted by anthropomorphic at 9:06 PM on October 7, 2009

"Jesus The Mexican Boy" Iron and Wine
"While You Were Sleeping" Elvis Perkins (doubly sad when you find out that his mom died in 9-11...)
"Still" Elvis Costello
"Long Black Veil" Dave Matthews (live)
"You are My Sunshine" Norman Blake
"Fred Jones (pt 2)" Ben Folds
"Evaporated" Ben Folds Five
"A Lack of Color" Death Cab for Cutie
"Ticking" Elton John
"Round the Bend" Beck
"Montague Terrace in Blue" Scott Walker
"If You Go Away" Scott Walker
"Woke up New" The Mountain Goats
"Black" Pearl Jam

nthing - Trapeze Swinger, Hallelujah, Casimir Pulaski Day, Radiohead, Nick Drake

I'm sure we could go on and on, but I think we're gonna go snuggle up with a box of tissues!
posted by ThaBombShelterSmith at 9:49 PM on October 7, 2009

Anathema - One Last Goodbye (and many others by them)
Smog - Rock Bottom Riser

seconding Leonard Cohen - Famous Blue Raincoat
posted by nemutdero at 10:07 PM on October 7, 2009

Mad World by Gary Jules makes me cry, but that might be because of the movie it's connected to.
posted by Gorgik at 10:41 PM on October 7, 2009

Richard Buckner has a lot to choose from. If I had to pick one, it'd be "Song of 27" from Devotion + Doubt (which has a few more songs that could be candidates for this thread, not to mention some songs from his other albums). Devastating, heart-wrenching and beautiful.
posted by rangefinder 1.4 at 12:47 AM on October 8, 2009

If you like Roberta Flack's version of "The First Time Ever I Saw Your Face" (which is great) you have to at least listen to the Peter, Paul, and Mary version too.
posted by dseaton at 2:17 AM on October 8, 2009 [1 favorite]

Goodnight, California - Kathleen Edwards
Whispering Pines - The Band (Dar Williams's version is quite good, too)
Sudden Waves - June Tabor
Brothers on a Hotel Bed - Death Cab for Cutie
By Piccadilly Station I Sat Down and Wept - Tracey Thorn
Latter Days, Suitcase- Over the Rhine
Moorestown - Sun Kil Moon (you can't really go wrong with Mark Kozelek in this mode)
Superwoman (Where Were You When I Needed You), Joy Inside My Tears - Stevie Wonder
Why Won't You Stay, Last Harbor - American Music Club (another "can't go wrong" artist for melancholia)
Almost anything off Big Star's Third or The Cure's Disintegration
posted by anthom at 7:39 AM on October 8, 2009

The first and last tracks of Time (The Revelator) by Gillian Welch.
posted by zennoshinjou at 8:07 AM on October 8, 2009

Iron & Wine's cover of Love Vigilantes.
posted by shannonm at 10:04 AM on October 8, 2009

shannonm's recommendation just reminded me: Grant Lee Phillips's covers of Age of Consent, So. Central Rain, and Boys Don't Cry are very lump-in-throat-provoking. (All of them available on his excellent covers album, nineteeneighties. The original So. Central Rain, of course, is no slouch when it comes to heartachingly beautiful.)

Also, Mockingbirds by his earlier band, Grant Lee Buffalo.
posted by scody at 11:13 AM on October 8, 2009

I'm a little late to the party, but in addition to Barcelona's "Please don't go" which was mentioned upthread, Dream Theater's "Disappear" has always struck me. Especially as I learned and experienced the true meaning of the song.
posted by odi.et.amo at 3:03 PM on October 8, 2009

Here Ya Go.
posted by wittgenstein at 8:20 PM on October 8, 2009

You people -- I want...more. This thread, this fragile, bird-ribbed thread, gently as it hums, must never end.

I want...more.
posted by Lipstick Thespian at 8:46 PM on October 8, 2009

There have been some grant electronica records that really have a melancholy feel to them:

Moby - Why Does My Heart Feel So Bad

Humate - Love Stimulation (Paul Van Dyk Remix)

Orbital - Belfast
posted by empath at 8:53 PM on October 8, 2009

Mazzy Star - Fade Into You
posted by empath at 9:03 PM on October 8, 2009 [1 favorite]

Well, I've already responded twice in this thread, but if you need more still, allow me to add 500 Miles, Peter Paul & Mary.
posted by DevilsAdvocate at 9:37 PM on October 8, 2009

This is gorgeous: Suitcase by Over The Rhine
posted by MeowForMangoes at 11:36 PM on October 8, 2009

A bit out of your aesthetic fields, but these always had a place in my "Wallow" playlist.

Wake Up - Arcade Fire

The Lady With The Braid - Dory Previn

Prom Theme - Fountains Of Wayne

Long Time Ago - White Magic

Glass Slipper - The Dresden Dolls

Half of "Blue Sunshine" by The Glove. Not the Robert Smith demo versions.
Pretty much half of The Magnetic Fields' 69 Love Songs. , I'm Sorry That I Love You.

And of course

Pasty Cline - Walkin' After Midnight (the moody version, without the backup singers)
posted by The Whelk at 8:17 AM on October 9, 2009

Also, a bit over the top, but you need that when you are Wallowing

I Don't Care Much - Cabaret Sdntk
posted by The Whelk at 8:25 AM on October 9, 2009

Here's a few more of my own to wet the blade:

any song from Campfire Headphase, by Boards of Canada (just TRY and not think about getting on an airport shuttle at 5am when listening to Dayvan Cowboy.)

Abdullah Ibrahim - anything from the Senzo release (gorgeous piano jazz designed to make you stare out windows for HOURS in sheer contemplation)

Cesaria Evora - Sodade
Band of Horses - The Funeral, and Is There A Ghost?

Ryan Adams - his cover of A Song For You, by Gram Parsons (if you cannot get weepy from this song, you were born with rocks for guts and should be put in a public park for the pigeons)

Stevie Nicks - Storms

Kristen Hersh - Your Ghost, from the Hips and Makers release

Carly Simon - That's The Way I Always Heard It Should Be

Donovan - Happiness Runs

Now go, minions, go - dig deep into your melancholy sweet pomegranate hearts and offer up your morsels to the wind!
posted by Lipstick Thespian at 9:26 AM on October 9, 2009

Well, there is Wilco's I am Trying to Break your Heart and She's a Jar and Via Chicago and Misunderstood and almost all of their pre-rehab stuff.
posted by holdkris99 at 1:58 PM on October 9, 2009

The Field Mice - So Said Kay
posted by bobobox at 7:22 PM on October 9, 2009

"Der Abschied" from Mahler's Das Lied von der Erde (This is only 1/3 of it; be sure to get the whole thing somewhere)

The third movement (part 2) from Shostakovich's 7th symphony

And, of course, Messiaen's Quartet for the End of Time. Composed in a concentration camp during World War II. Best taken as a whole, but here's the eighth, final, movement.

(watch all of these in high quality if you can; the audio is much better)
posted by clorox at 12:38 AM on October 10, 2009

Nickle Creek's Out of the Woods always gets to me.
So does:
Shotgun Down The Avalanche by Shawn Colvin.
We Belong Together Rickie Lee Jones
The Dark End of The Street James Carr
Embryonic Journey Jefferson Airplane
posted by dpcoffin at 3:02 PM on October 10, 2009

I made a melancholia themed mix a while ago. Mostly 'world music'.
posted by dhruva at 3:41 PM on October 10, 2009

Ryan Adams' cover of Stars Go Blue is usually too much for me to handle. I ran out of a hipster jewelry store when that the song came on. It sounds spare in the beginning, and then a female voice lifts it up out of nowhere.

Bon Iver's For Emma and Skinny Love, as already recommended. Seconding Radiohead's No Surprises, as well.

Horse Feathers's (same vein as Bon Iver) Rude to Rile.

Okkervil River used to be much sadder, and I'm personally a sucker for sad songs about mothers, like Red.

Julie Doiron is known for her quiet, wintry, French music. Le Piano is pretty indicative of her style.

I'm totally shocked no one has rec'd Have You Forgotten by Red House Painters.

Antony & The Johnsons are widely known for their emotive, weird, tragic songs.

Belle & Sebastian's Piazza, New York Catcher is a must.

You know, it sounds upbeat, but that's why it hurts to listen to it, like when your mom smiles at your grandma's funeral so you don't see her cry: Camera Obscura's Hey Lloyd, I'm Ready to Be Heartbroken.

CocoRosie's cover of Ohio is devastating. If you're a CocoRosie hater, it's a cover of a Damien Jurado song.

Regina Spektor's Samson.

Neil Young's Only Love Can Break Your Heart is roundly criticized for being his cheesiest song, but it's so damn sad!

Rilo Kiley wrote much sadder song in their early days, such as Wires and Waves and Pictures of Success on the album Take Offs and Landings.
posted by zoomorphic at 7:25 PM on October 10, 2009

Dark End of the Street working…
posted by dpcoffin at 12:30 PM on October 11, 2009 [1 favorite]

oh, how can I forget Daniel, by Elton John?

or even Faithfully, or even Wheels in the Sky by Journey? (okay that's definitely at the outer limits of acceptability in this category, but on the right day those two songs will flatten ya.)

The Chain, by Fleetwood Mac

Maybe even Wake Up Alone, by Amy Winehouse, if'n you're in the right mood?

More, great sweet sobbing hivemind, you must marinate me on this grill of this thread!
posted by Lipstick Thespian at 7:06 PM on October 11, 2009

Tears in Heaven, by Eric Clapton - especially poignant because it's about his son, who died tragically at a young age.
posted by SuperSquirrel at 7:31 PM on October 11, 2009

Not really Sad, but always makes me cry

Pogo - Go Out and Love Someone.
posted by The Whelk at 9:19 PM on October 11, 2009

Thousands Are Sailing by the Pogues. Lyrics.

Another Rilo Kiley recommendation: The Absence of God.
posted by ibmcginty at 9:34 AM on October 12, 2009

The Searchers - What Have They Done To The Rain?
posted by Lipstick Thespian at 8:04 PM on October 12, 2009

Way freakin' late to add another song, but Richard Buckner's "Lil Wallet Picture"...well, let's just say the only time my wife pays attention to my guitar noodling is when I try to play that song...so she can tell me not to play it. It's just that devastating.
posted by notsnot at 6:41 AM on October 13, 2009

White Room, by Cream.
posted by Kronos_to_Earth at 1:52 PM on October 14, 2009

Don't Give Up, by Peter Gabriel and Kate Bush!

Keep 'em coming people, this great sexy sobfest will not go gently into that electronic night!
posted by Lipstick Thespian at 7:43 PM on October 14, 2009

This is where I show how square my tastes are.

Perfect Fit - Dresden Dolls

Papa Was A Rodeo - Magnetic Fields

Here Comes Mary - The Raveonettes


I Will Wait For you - Connie Francis

What Is This Thing Called Love? - Frank Sinatra

Will You Still Love Tomorrow? - Dusty Springfield

Save The Last Dance For Me - The Drifters

Somewhere Over The Rainbow
posted by The Whelk at 8:01 PM on October 14, 2009

Lemon Haired Ladies - Dory Previn
posted by The Whelk at 8:06 PM on October 14, 2009

The Killing Moon - Echo And The Bunnymen cause like, duh.
posted by The Whelk at 8:10 PM on October 14, 2009

And for personal reasons of wallowing

What Ever Happened? - The Strokes


Out On The Streets - Blondie


Keep It Hid - Alice Clark


The Queen And The Soldier - Suzanne Vega
posted by The Whelk at 8:16 PM on October 14, 2009

Thirding the rec for Neutral Milk Hotel and specifically their song "Aeroplane Over the Sea" which always tears me apart.
posted by darkstar at 9:11 PM on October 14, 2009

The Whelk - I should vaporize you for that Alice Clark song. You obviously have too much power over my emotional states and require neutralization for the good of all.
posted by Lipstick Thespian at 3:28 PM on October 15, 2009

The Low Anthem - (Don't) Trouble
posted by Lipstick Thespian at 10:59 AM on October 18, 2009

I keep thinking to add this, now I'm here, so:
Winter Song - Emily Smith

Always reminds me of this one…
Urge for Going - Tom Rush
posted by dpcoffin at 7:52 PM on October 19, 2009

"Pony" - Tom Waits
posted by LakesideOrion at 11:11 AM on October 29, 2009

Dream River - The Mavericks
posted by mikepop at 6:05 PM on November 5, 2009

Camera Obscura - Country Mile
Doves - A House
Martin Grech - Open Heart Zoo

But it's Kent - Vi Kan Väl Vänta Tills Imorgon which gets me every time.
posted by tzb at 7:42 AM on December 30, 2009

Eddie Vedder: No Ceiling
posted by JakeBarnes at 7:19 PM on February 26, 2010

Oh, and In My Life: The Beatles. Best of the best right here.
posted by JakeBarnes at 7:21 PM on February 26, 2010

Mountain Goats - No Children

Kiki and Herb so a great cover of this but I can't find it online
posted by The Whelk at 7:24 PM on February 26, 2010

For me:

Elbow - Station Approach
Fionn Regan - Put A Penny in the Slot
Ed Harcourt - Black Dress (it's a happy kind of sad and one I listened to a lot when MrMippy and I met)
posted by mippy at 4:34 AM on August 26, 2010